NPASS Compound

Natural Product: NPC475140

Natural Product ID	NPC475140
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Mirabilin
IUPAC Name	(2S,4aS,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-4a-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2-carboxylic acid
Synonyms	Mirabilin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL499264
PubChem CID	44566610
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 180189 0 0 0 0 0 0 0 0999 V2000 1.0105 -10.6135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -9.1362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4895 -7.6590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -6.1818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 -5.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -4.2535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -4.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 -3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 -2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -3.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7181 -5.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3086 -5.7307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -6.6949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -6.6949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 -7.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6382 -8.5069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 -9.8060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6486 -11.2832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9091 -12.7604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7600 -13.7246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9091 -14.6887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6486 -16.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9091 -17.6432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1696 -19.1204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2391 -16.6790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0900 -15.7148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3505 -14.2376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0900 -12.7604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6805 -15.2018 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0900 -17.6432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8882 -9.8060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6382 -8.5069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8882 -7.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6277 -5.7307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7768 -4.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5268 -6.0655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0268 -6.0655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7768 -4.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0268 -3.4675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5268 -3.4675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1172 -2.9544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7663 -1.9902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9258 -3.8023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7872 -7.5427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2977 -10.3190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 -2.7762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -1.8121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3405 9.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0105 10.5705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9875 11.6675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4200 11.0835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7500 6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2500 6.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1491 6.1603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8086 -5.7307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0691 -7.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 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H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2877 5.0949 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1528 5.2973 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2811 5.1762 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2044 3.9224 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0377 1.1977 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4816 2.3635 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6337 3.9576 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3086 -5.7307 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8191 -8.5069 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3340 -9.5528 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8086 -10.6135 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6277 -7.6590 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4786 -3.7404 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 11 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 25 30 1 0 17 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 32 44 1 0 31 45 1 0 8 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 52 54 1 0 51 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 2 0 61 62 1 0 62 63 1 1 62 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 69 70 1 1 69 71 1 0 71 72 1 0 69 73 1 0 73 74 2 0 73 75 1 0 66 76 1 6 76 77 1 0 65 78 1 0 57 79 1 6 50 80 1 6 5 81 1 0 81 82 1 0 82 83 1 0 83 84 1 0 82 85 1 0 81 86 1 0 83 3 1 0 12 7 1 0 33 15 1 0 40 35 1 0 52 47 1 0 62 57 1 0 72 66 1 0 27 20 1 0 58 50 1 0 67 61 1 0 1 87 1 0 2 88 1 0 2 89 1 0 3 90 1 1 5 91 1 1 7 92 1 6 8 93 1 1 10 94 1 0 10 95 1 0 11 96 1 1 12 97 1 1 13 98 1 0 15 99 1 6 17100 1 6 18101 1 0 18102 1 0 20103 1 1 22104 1 1 23105 1 0 23106 1 0 24107 1 0 25108 1 6 26109 1 1 27110 1 6 28111 1 0 29112 1 0 30113 1 0 31114 1 1 32115 1 6 33116 1 1 35117 1 6 37118 1 0 37119 1 0 38120 1 6 39121 1 6 40122 1 1 41123 1 0 42124 1 0 43125 1 0 44126 1 0 45127 1 0 47128 1 1 48129 1 0 48130 1 0 49131 1 0 49132 1 0 51133 1 1 53134 1 0 53135 1 0 53136 1 0 54137 1 0 54138 1 0 54139 1 0 55140 1 0 55141 1 0 56142 1 0 56143 1 0 58144 1 1 59145 1 0 59146 1 0 60147 1 0 63148 1 0 63149 1 0 63150 1 0 64151 1 0 64152 1 0 65153 1 6 67154 1 6 68155 1 0 68156 1 0 70157 1 0 70158 1 0 70159 1 0 71160 1 0 71161 1 0 72162 1 0 72163 1 0 75164 1 0 76165 1 0 76166 1 0 77167 1 0 78168 1 0 79169 1 0 79170 1 0 79171 1 0 80172 1 0 80173 1 0 80174 1 0 81175 1 6 82176 1 1 83177 1 6 84178 1 0 85179 1 0 86180 1 0 M END

Standard InCHIKey	PJRGLLVWCPCORC-SAMSJERTSA-N
Standard InCHI	InChI=1S/C58H94O28/c1-53(2)30-9-12-56(5)31(8-7-23-24-15-54(3,52(75)76)13-14-58(24,22-61)32(63)16-57(23,56)6)55(30,4)11-10-33(53)84-50-45(86-49-44(74)40(70)36(66)27(18-60)81-49)38(68)29(21-79-50)83-51-46(85-48-42(72)34(64)25(62)19-77-48)41(71)37(67)28(82-51)20-78-47-43(73)39(69)35(65)26(17-59)80-47/h7,24-51,59-74H,8-22H2,1-6H3,(H,75,76)/t24-,25-,26+,27+,28+,29-,30-,31+,32+,33-,34-,35+,36+,37+,38-,39-,40-,41-,42+,43+,44+,45+,46+,47+,48-,49-,50-,51-,54-,55-,56+,57+,58+/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@@H](OC[C@@H]([C@@H]2O)O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)[C@H]([C@@H]([C@H]2O[C@@H]2OC[C@@H]([C@@H]([C@H]2O)O)O)O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)C[C@H]([C@@]2([C@H]3C[C@](C)(CC2)C(=O)O)CO)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1238.59	Volume:	1167.012 ? Van der Waals volume.
Dense:	1.061	LogP:	-1.605 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.094 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.495 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	57.0
TPSA:	453.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	28.0
H-Bond Donor:	17.0	Rings:	10.0
Heavy Atoms:	28.0

MedChem Properties

QED Drug-Likeness Score:	0.054	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.358	Fsp³:	0.948
MCE-18:	218.124 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.678	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.376	Promiscuous compounds:	0.146

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.305	MDCK Permeability:	-4.882
Pgp-inhibitor:	0.0	Pgp-substrate:	0.959
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.848
20% Bioavailability (F20%):	0.936	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016	MRP1:	0.03
Plasma Protein Binding (PPB):	43.082%	Volume Distribution (VD):	-0.411
Fu:	41.122% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.961	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.469
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.116
HLM stability:	0.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

-0.822

Half-life (T1/2):

4.226

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.735	Drug-induced Liver Injury (DILI):	0.978
AMES Toxicity:	0.993	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.093	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.888	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.325	RPMI-8226 Immunitoxicity:	0.353
A549 Cytotoxicity:	0.994	Hek293 Cytotoxicity:	0.616
BCF:	0.761 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.385 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.942 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.749 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO15237	Cyclamen mirabile	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9090874]
NPO15237	Cyclamen mirabile	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15237	Cyclamen mirabile	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	4
Activity	2

Activity Type	# Activity
Organism	4
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	0.7	10'-6M	PMID[9090874]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	1.1	10'-6M	PMID[9090874]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	400.0	ug.mL-1	PMID[21476569]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	400.0	ug.mL-1	PubChem BioAssay data set
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	400.0	ug.mL-1	PMID[18990572]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	400.0	ug.mL-1	PMID[22047694]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC475140 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	24224
0.1-0.2	21340
0.2-0.3	2968
0.3-0.4	655
0.4-0.5	466
0.5-0.6	163
0.6-0.7	24
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8611	High Similarity	NPC151543
0.7304	Intermediate Similarity	NPC185466
0.6991	Remote Similarity	NPC123796
0.6957	Remote Similarity	NPC291903
0.6949	Remote Similarity	NPC473824
0.6864	Remote Similarity	NPC475119
0.6864	Remote Similarity	NPC288205
0.6864	Remote Similarity	NPC51465
0.6695	Remote Similarity	NPC207738
0.6667	Remote Similarity	NPC610204
0.6639	Remote Similarity	NPC603137
0.6557	Remote Similarity	NPC471384
0.6525	Remote Similarity	NPC606145
0.6504	Remote Similarity	NPC166422
0.6271	Remote Similarity	NPC257468
0.626	Remote Similarity	NPC610461
0.6174	Remote Similarity	NPC488561
0.6148	Remote Similarity	NPC609281
0.6129	Remote Similarity	NPC607904
0.6098	Remote Similarity	NPC606553
0.6083	Remote Similarity	NPC471435
0.6083	Remote Similarity	NPC471434
0.6083	Remote Similarity	NPC302887
0.6066	Remote Similarity	NPC488564
0.6033	Remote Similarity	NPC37134
0.6032	Remote Similarity	NPC323341
0.5983	Remote Similarity	NPC80843
0.595	Remote Similarity	NPC488515
0.595	Remote Similarity	NPC484832
0.5948	Remote Similarity	NPC127056
0.5859	Remote Similarity	NPC219180
0.5859	Remote Similarity	NPC609305
0.5854	Remote Similarity	NPC481079
0.5833	Remote Similarity	NPC104400
0.5833	Remote Similarity	NPC10320
0.5814	Remote Similarity	NPC283417
0.5814	Remote Similarity	NPC200049
0.5785	Remote Similarity	NPC105800
0.5785	Remote Similarity	NPC139044
0.5781	Remote Similarity	NPC243680
0.5763	Remote Similarity	NPC470512
0.5763	Remote Similarity	NPC488516
0.5758	Remote Similarity	NPC265841
0.5758	Remote Similarity	NPC488308
0.5739	Remote Similarity	NPC164194
0.5735	Remote Similarity	NPC488309
0.5726	Remote Similarity	NPC323359
0.5714	Remote Similarity	NPC271610
0.5714	Remote Similarity	NPC312650
0.5691	Remote Similarity	NPC79718
0.5691	Remote Similarity	NPC119794
0.5672	Remote Similarity	NPC471385
0.5669	Remote Similarity	NPC172365
0.5659	Remote Similarity	NPC284449
0.5649	Remote Similarity	NPC54636
0.5643	Remote Similarity	NPC33012
0.5635	Remote Similarity	NPC475486
0.5625	Remote Similarity	NPC200788
0.562	Remote Similarity	NPC117714
0.562	Remote Similarity	NPC30289
0.561	Remote Similarity	NPC470514
0.56	Remote Similarity	NPC324875
0.56	Remote Similarity	NPC292677
0.56	Remote Similarity	NPC75318
0.5591	Remote Similarity	NPC473688
0.5591	Remote Similarity	NPC280941
0.5591	Remote Similarity	NPC470915
0.5591	Remote Similarity	NPC235772
0.5583	Remote Similarity	NPC76497
0.5583	Remote Similarity	NPC469946
0.5581	Remote Similarity	NPC126753
0.5574	Remote Similarity	NPC488526
0.5574	Remote Similarity	NPC173859
0.5574	Remote Similarity	NPC232237
0.5571	Remote Similarity	NPC8524
0.5565	Remote Similarity	NPC64715
0.5556	Remote Similarity	NPC160452
0.5537	Remote Similarity	NPC469945
0.5528	Remote Similarity	NPC63159
0.552	Remote Similarity	NPC145899
0.552	Remote Similarity	NPC78034
0.5492	Remote Similarity	NPC114304
0.5489	Remote Similarity	NPC4749
0.5484	Remote Similarity	NPC73829
0.5484	Remote Similarity	NPC470513
0.5481	Remote Similarity	NPC470876
0.5476	Remote Similarity	NPC301449
0.5476	Remote Similarity	NPC601290
0.547	Remote Similarity	NPC1046
0.5469	Remote Similarity	NPC210729
0.5469	Remote Similarity	NPC82931
0.5468	Remote Similarity	NPC250247
0.5462	Remote Similarity	NPC25605
0.5462	Remote Similarity	NPC59804
0.5455	Remote Similarity	NPC602995
0.5396	Remote Similarity	NPC482010
0.5391	Remote Similarity	NPC104137
0.5391	Remote Similarity	NPC31838
0.5391	Remote Similarity	NPC26626
0.5379	Remote Similarity	NPC123199
0.5372	Remote Similarity	NPC472949
0.536	Remote Similarity	NPC481082
0.536	Remote Similarity	NPC164419
0.536	Remote Similarity	NPC297263
0.5338	Remote Similarity	NPC470218
0.5338	Remote Similarity	NPC191827
0.5333	Remote Similarity	NPC309780
0.5333	Remote Similarity	NPC56713
0.5328	Remote Similarity	NPC263756
0.5328	Remote Similarity	NPC213674
0.5328	Remote Similarity	NPC476779
0.5323	Remote Similarity	NPC164389
0.5323	Remote Similarity	NPC148603
0.5323	Remote Similarity	NPC480475
0.5304	Remote Similarity	NPC242611
0.5303	Remote Similarity	NPC470911
0.5294	Remote Similarity	NPC476774
0.5294	Remote Similarity	NPC476780
0.529	Remote Similarity	NPC136768
0.529	Remote Similarity	NPC110700
0.529	Remote Similarity	NPC476777
0.5289	Remote Similarity	NPC480424
0.5286	Remote Similarity	NPC220160
0.528	Remote Similarity	NPC471383
0.5276	Remote Similarity	NPC470914
0.5276	Remote Similarity	NPC77717
0.5274	Remote Similarity	NPC475177
0.5271	Remote Similarity	NPC138219
0.5271	Remote Similarity	NPC475234
0.5263	Remote Similarity	NPC470622
0.5263	Remote Similarity	NPC251263
0.5259	Remote Similarity	NPC85154
0.5252	Remote Similarity	NPC309223
0.5252	Remote Similarity	NPC302543
0.525	Remote Similarity	NPC136877
0.5242	Remote Similarity	NPC204392
0.5242	Remote Similarity	NPC309714
0.5242	Remote Similarity	NPC605226
0.5235	Remote Similarity	NPC329893
0.5231	Remote Similarity	NPC11242
0.5227	Remote Similarity	NPC123522
0.5227	Remote Similarity	NPC79643
0.5226	Remote Similarity	NPC23020
0.5226	Remote Similarity	NPC488619
0.5221	Remote Similarity	NPC21691
0.5217	Remote Similarity	NPC161717
0.5217	Remote Similarity	NPC31839
0.5211	Remote Similarity	NPC102505
0.5211	Remote Similarity	NPC488514
0.52	Remote Similarity	NPC44716
0.52	Remote Similarity	NPC264270
0.5197	Remote Similarity	NPC300655
0.5197	Remote Similarity	NPC13989
0.5197	Remote Similarity	NPC196874
0.5195	Remote Similarity	NPC478559
0.5195	Remote Similarity	NPC478560
0.5185	Remote Similarity	NPC25663
0.5175	Remote Similarity	NPC283849
0.5175	Remote Similarity	NPC606107
0.517	Remote Similarity	NPC489208
0.5156	Remote Similarity	NPC276093
0.5154	Remote Similarity	NPC481078
0.5154	Remote Similarity	NPC187290
0.5143	Remote Similarity	NPC476991
0.5126	Remote Similarity	NPC90856
0.5111	Remote Similarity	NPC470517
0.5108	Remote Similarity	NPC484059
0.5108	Remote Similarity	NPC484060
0.5108	Remote Similarity	NPC43550
0.5106	Remote Similarity	NPC476775
0.5079	Remote Similarity	NPC251768
0.5077	Remote Similarity	NPC488209
0.5076	Remote Similarity	NPC51579
0.5072	Remote Similarity	NPC13998
0.507	Remote Similarity	NPC51564
0.5069	Remote Similarity	NPC489209
0.5067	Remote Similarity	NPC484831
0.5067	Remote Similarity	NPC40085
0.5064	Remote Similarity	NPC222951
0.5041	Remote Similarity	NPC48499
0.5041	Remote Similarity	NPC109079
0.5041	Remote Similarity	NPC482748
0.504	Remote Similarity	NPC112352
0.5039	Remote Similarity	NPC118440
0.5037	Remote Similarity	NPC135904
0.5036	Remote Similarity	NPC71391
0.5036	Remote Similarity	NPC192765
0.5035	Remote Similarity	NPC279915
0.5035	Remote Similarity	NPC476778

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC475140 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7079
0.1-0.2	2022
0.2-0.3	43
0.3-0.4	4
0.4-0.5	2
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data